Dichloromethane → HCID 25022748, compound

HRID 564297Notes

Reaction equation

HRID 564297 reaction equation
Cl[P:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N([CH2:20][CH3:21])CC)C.[CH3:22][O:23][CH2:24][CH2:25][NH2:26].C(Cl)Cl>C1(C)C=CC=CC=1>[P:2]([N:26]([P:2]([C:21]1[CH:20]=[CH:14][CH:9]=[CH:10][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:25][CH2:24][O:23][CH3:22])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 66180Chlorodiphenylphosphine

Product 1

HCID 25022748HCID 25022748, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chlorodiphenylphosphine (4.5 mL, 24 mmol, 2.3 equiv.) was dissolved in dry toluene (150 mL). Under an atmosphere of argon, an excess of triethylamine (5.0 mL, 36 mmol) was syringed into the reaction flask, which was stirred for 5 minutes. 2-Methoxyethylamine (0.9 mL, 10 mmol) was then syringed dropwise under argon. A precipitate immediately formed. The reaction mixture was then allowed to stir for 36 hrs at 110° C. The ammonium salt was filtered off and the solvent and the excess triethylamine and diphenylphosphine were removed in vacuo to leave a yellow residue. The residue was passed through a silica gel plug using a CH2Cl2 (15%)/petroleum ether (85%) mixture as the eluent. Removing the solvent afforded 2.905 g of a fine white powder in 63% yield. 1H NMR (RT, 300 MHz, CDCl3): δ=2.90 (2H, t, JHH=7.4 Hz, CH2O), 3.02 (3H, s, OCH3), 3.47 (2H, m, CH2), 7.29-7.44 (20H, m, ArH). 31P NMR (RT, 121 MHz, CDCl3): δ=64.6 ppm (s). MS (FAB+): 444 (M+H).

Workup

  1. customA precipitate immediately formed
  2. stirringto stir for 36 hrs at 110° C
  3. filtrationThe ammonium salt was filtered off
  4. customthe solvent and the excess triethylamine and diphenylphosphine were removed in vacuo
  5. customto leave a yellow residue
  6. customRemoving the solvent

Sources & evidence

ORD record
ord-19acc1a2275d4a59b9a9c8eb2ceeb0e9
Source dataset
uspto-grants-2011_11
Patent number
US08067654B2

Reaction notes

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